Career: 1986-2000
'90s Team(s): Detroit Pistons (1990-93), San Antonio Spurs (1993-95), Chicago Bulls (1995-98), Los Angeles Lakers (1999)

Dennis Rodman’s an “alcoholic” which partially explains his money problems (the other being that he’s Dennis Rodman). That means since his career ended he has been trapped in reality TV hell. From Celebrity Mole (which he won) to Celebrity Rehab to Celebrity Apprentice, twice.

He also found himself trapped in the cable news cycle this year when he visited North Korea as part of a promotion for Vice Media. It was the first time Kim Jong-un had seen an American in person (think about the first time you saw snow). Regardless, Dennis referred to the “leader” as a “friend for life,” an "awesome dude" and suggested President Obama call him to squash a potential future war because they both like hoops. Then he came back and stated he should win the Nobel Peace Prize. We like his odds.